U.S. patent application number 13/326402 was filed with the patent office on 2012-12-20 for heterocyclic compound and organic light-emitting device containing same.
Invention is credited to Se-Jin Cho, Sang-Hyun Han, Seok-Hwan Hwang, Hye-Jin Jung, Young-Kook Kim, Yoon-Hyun Kwak, Jong-Hyuk Lee, Sun-Young Lee, Jin-O Lim.
Application Number | 20120319087 13/326402 |
Document ID | / |
Family ID | 47228606 |
Filed Date | 2012-12-20 |
United States Patent
Application |
20120319087 |
Kind Code |
A1 |
Lee; Sun-Young ; et
al. |
December 20, 2012 |
HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE CONTAINING
SAME
Abstract
A heterocyclic compound, organic light-emitting device, and a
flat panel display device, the heterocyclic compound being
represented by Formula 1 or 2 below: ##STR00001##
Inventors: |
Lee; Sun-Young;
(Yongin-City, KR) ; Hwang; Seok-Hwan;
(Yongin-City, KR) ; Kim; Young-Kook; (Yongin-City,
KR) ; Kwak; Yoon-Hyun; (Yongin-City, KR) ;
Jung; Hye-Jin; (Yongin-City, KR) ; Lim; Jin-O;
(Yongin-City, KR) ; Lee; Jong-Hyuk; (Yongin-City,
KR) ; Han; Sang-Hyun; (Yongin-City, KR) ; Cho;
Se-Jin; (Yongin-City, KR) |
Family ID: |
47228606 |
Appl. No.: |
13/326402 |
Filed: |
December 15, 2011 |
Current U.S.
Class: |
257/40 ;
257/E51.019; 544/180; 544/333; 546/77 |
Current CPC
Class: |
C09K 11/06 20130101;
C07D 401/14 20130101; C07D 221/18 20130101; C09K 2211/1044
20130101; C09K 2211/1092 20130101; C07D 409/10 20130101; C07D
471/04 20130101; C09K 2211/1029 20130101; H01L 51/0072 20130101;
H01L 51/5012 20130101; C07D 401/10 20130101 |
Class at
Publication: |
257/40 ; 546/77;
544/180; 544/333; 257/E51.019 |
International
Class: |
H01L 51/54 20060101
H01L051/54; C07D 471/04 20060101 C07D471/04; C07D 409/10 20060101
C07D409/10; C07D 401/10 20060101 C07D401/10; C07D 221/18 20060101
C07D221/18; C07D 401/14 20060101 C07D401/14 |
Foreign Application Data
Date |
Code |
Application Number |
Jun 16, 2011 |
KR |
10-2011-0058633 |
Claims
1. A heterocyclic compound represented by Formula 1 or Formula 2
below: ##STR00041## wherein R.sub.1 to R.sub.5 are each
independently selected from the group of a hydrogen atom, a heavy
hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a
substituted or unsubstituted C2-C60 alkenyl group, a substituted or
unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted
C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60
alkoxy group, a substituted or unsubstituted C5-C60 aryloxy group,
a substituted or unsubstituted C5-C60 arylthio group, a substituted
or unsubstituted C5-C60 aryl group, a substituted or unsubstituted
C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60
condensed polycyclic group, a halogen atom, a cyano group, a nitro
group, a hydroxy group, a carboxy group, and an amino group
substituted with a C5-C60 aryl group or a C3-C60 heteroaryl group;
##STR00042## wherein R.sub.6 to R.sub.10 are each independently
selected from the group of a hydrogen atom, a heavy hydrogen atom,
a substituted or unsubstituted C1-C60 alkyl group, a substituted or
unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted
C2-C60 alkynyl group, a substituted or unsubstituted C3-C60
cycloalkyl group, a substituted or unsubstituted C1-C60 alkoxy
group, a substituted or unsubstituted C5-C60 aryloxy group, a
substituted or unsubstituted C5-C60 arylthio group, a substituted
or unsubstituted C5-C60 aryl group, a substituted or unsubstituted
C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60
condensed polycyclic group, a halogen atom, a cyano group, a nitro
group, a hydroxy group, a carboxy group, and an amino group
substituted with a C5-C60 aryl group or a C3-C60 heteroaryl
group.
2. The heterocyclic compound of claim 1, wherein R.sub.1 to
R.sub.10 are each independently selected from the group of a
hydrogen atom, a heavy hydrogen atom, a cyano group, a halogen
atom, a substituted or unsubstituted C1-C20 alkyl group, a
substituted or unsubstituted C5-C40 aryl group, a substituted or
unsubstituted C3-C40 heteroaryl group, a substituted or
unsubstituted C6-C40 condensed polycyclic group, and an amino group
substituted with a C5-C40 aryl group or a C3-C20 heteroaryl
group.
3. The heterocyclic compound of claim 1, wherein R.sub.1 to
R.sub.10 are each independently selected from the group of a
hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a C1-C20 alkyl group, and compounds represented by Formulae
2a to 2g below: ##STR00043## wherein Q.sub.1 is selected from the
group of linking groups represented by --C(R.sub.11)(R.sub.12)--,
--N(R.sub.13)--, --S--, and --O--; Y.sub.1, Y.sub.2, and Y.sub.3
are each independently selected from the group of linking groups
represented by --N.dbd. and --C(R.sub.14).dbd.; Z.sub.1, Z.sub.2,
Ar.sub.12, Ar.sub.13, R.sub.11, R.sub.12, R.sub.13, and R.sub.14
are each independently selected from the group of a hydrogen atom,
a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl
group, a substituted or unsubstituted C5-C20 aryl group, a
substituted or unsubstituted C3-C20 heteroaryl group, a substituted
or unsubstituted C6-C20 condensed polycyclic group, a halogen atom,
a cyano group, a nitro group, a hydroxy group, and a carboxy group;
Ar.sub.11 is selected from the group of a substituted or
unsubstituted C1-C20 alkylene group, a substituted or unsubstituted
C5-C20 arylene group, and a substituted or unsubstituted C3-C20
heteroarylene group; p is an integer from 1 to 12; r is an integer
from 0 to 5; and * is a binding site.
4. The heterocyclic compound of claim 1, wherein R.sub.1 to
R.sub.10 are each independently selected from the group of a
hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a methyl group, an ethyl group, a propyl group, a butyl
group, a pentyl group, and compounds represented by Formulae 3a to
3d below: ##STR00044## wherein Z.sub.1 is selected from the group
of a hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group; p is an integer from 1 to 12; and * is
a binding site.
5. The heterocyclic compound of claim 1, wherein: R.sub.1, R.sub.2,
R.sub.6, and R.sub.7 are each independently selected from the group
of a hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, and R.sub.3, R.sub.4, R.sub.5, R.sub.8, R.sub.9,
and R.sub.10 are each independently selected from the group of a
hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a C1-C20 alkyl group, and compounds represented by Formulae
2a to 2g below: ##STR00045## wherein Q.sub.1 is selected from the
group of linking groups represented by --C(R.sub.11)(R.sub.12)--,
--N(R.sub.13)--, --S--, and --O--; Y.sub.1, Y.sub.2, and Y.sub.3
are each independently selected from the group of linking groups
represented by --N.dbd. and --C(R.sub.14).dbd.; Z.sub.1, Z.sub.2,
Ar.sub.12, Ar.sub.13, R.sub.11, R.sub.12, R.sub.13, and R.sub.14
are each independently selected from the group of a hydrogen atom,
a heavy hydrogen atom, a substituted or unsubstituted C1-C20 alkyl
group, a substituted or unsubstituted C5-C20 aryl group, a
substituted or unsubstituted C3-C20 heteroaryl group, a substituted
or unsubstituted C6-C20 condensed polycyclic group, a halogen atom,
a cyano group, a nitro group, a hydroxy group, and a carboxy group;
Ar.sub.11 is selected from the group of a substituted or
unsubstituted C1-C20 alkylene group, a substituted or unsubstituted
C5-C20 arylene group, and a substituted or unsubstituted C3-C20
heteroarylene group; p is an integer from 1 to 12; and r is an
integer from 0 to 5; and * is a binding site.
6. The heterocyclic compound of claim 1, wherein: R.sub.1, R.sub.2,
R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.9, and R.sub.10 are each
independently selected from the group of a hydrogen atom, a heavy
hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group,
and a substituted or unsubstituted C5-C20 aryl group, and R.sub.3
and R.sub.8 are each independently selected from the group of a
hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a methyl group, an ethyl group, a propyl group, a butyl
group, a pentyl group, and compounds represented by Formulae 3a to
3d below: ##STR00046## wherein Z.sub.1 is selected from the group
of a hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group; p is an integer from 1 to 12; and * is
a binding site.
7. The heterocyclic compound of claim 1, wherein: R.sub.1, R.sub.2,
R.sub.6, and R.sub.7 are each independently a methyl group or a
phenyl group, and R.sub.3, R.sub.4, R.sub.5, R.sub.8, R.sub.9, and
R.sub.10 are each independently selected from the group of a
hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a methyl group, an ethyl group, a propyl group, a butyl
group, a pentyl group, and compounds selected from the group of
Formulae 3a to 3d below: ##STR00047## wherein Z.sub.1 is selected
from the group of a hydrogen atom, a heavy hydrogen atom, a
substituted or unsubstituted C1-C20 alkyl group, a substituted or
unsubstituted C5-C20 aryl group, a substituted or unsubstituted
C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20
condensed polycyclic group, a halogen atom, a cyano group, a nitro
group, a hydroxy group, and a carboxy group; p is an integer from 1
to 12; and * is a binding site.
8. The heterocyclic compound of claim 1, wherein the compound
represented by Formula 1 or Formula 2 includes a compound
represented by Compound 2, 16, 21, 24, 25, or 45, below.
##STR00048##
9. An organic light-emitting device, comprising: a first electrode;
a second electrode; and an organic layer interposed between the
first electrode and the second electrode, wherein the organic layer
includes the heterocyclic compound as claimed in claim 1.
10. The organic light-emitting device of claim 9, wherein the
organic layer includes a hole injection layer, a hole transport
layer, a single layer having both hole injecting and transporting
capabilities, an electron injection layer, an electron transport
layer, or a single layer having both electron injecting and
transporting capabilities.
11. The organic light-emitting device of claim 9, wherein the
organic layer is an emission layer and the heterocyclic compound is
a host or dopant for a fluorescent or phosphorescent device.
12. The organic light-emitting device of claim 9, wherein: the
organic layer includes an emission layer, a hole transport layer,
and an electron transport layer, and the emission layer includes an
anthracene compound, an arylamine compound, or a styryl
compound.
13. The organic light-emitting device of claim 9, wherein: the
organic layer includes an emission layer, a hole transport layer,
and an electron transport layer, and one of a red, a green, a blue,
and a white layer of the emission layer includes a phosphorescent
compound.
14. The organic light-emitting device of claim 9, wherein the
organic layer is a blue emission layer.
15. The organic light-emitting device of claim 9, wherein: the
organic layer is a blue emission layer, and the heterocyclic
compound is a blue host.
16. The organic light-emitting device of claim 9, wherein: the
organic layer includes a plurality of layers, and at least one
layer of the organic layer is formed by a wet process using the
heterocyclic compound.
17. A flat panel display device comprising the organic
light-emitting device as claimed in claim 9, wherein the first
electrode of the organic light-emitting device is electrically
connected to a source electrode or a drain electrode of a thin film
transistor.
Description
CROSS-REFERENCE TO RELATED PATENT APPLICATION
[0001] This application claims the benefit of Korean Patent
Application No. 10-2011-0058633, filed on Jun. 16, 2011, in the
Korean Intellectual Property Office, the disclosure of which is
incorporated herein in its entirety by reference.
BACKGROUND
[0002] 1. Field
[0003] Embodiments relate to a heterocyclic compound and an organic
light-emitting device including the heterocyclic compound.
[0004] 2. Description of the Related Art
[0005] Light-emitting devices are self-emission type display
devices that have a wide viewing angle, a high contrast ratio, and
a short response time. Due to these characteristics, light-emitting
devices are drawing more attention. Such light-emitting devices may
be roughly classified into inorganic light-emitting devices that
include emission layers containing inorganic compounds, and organic
light-emitting devices that include emission layers containing
organic compounds. For example, organic light-emitting devices may
have higher brightness, lower driving voltages, and shorter
response times than inorganic light-emitting devices, and may
render multi-colored displays. Thus, much research into such
organic light-emitting devices has been conducted. Generally, an
organic light-emitting device may have a stack structure including
an anode, a cathode, and an organic emission layer interposed
therebetween. However, a hole injection layer and/or a hole
transport layer may be further stacked between the anode and the
organic emission layer, and/or an electron transport layer may be
further stacked between the organic emission layer and the cathode.
For example, an organic light-emitting device may have a stack
structure of anode/hole transport layer/organic emission
layer/cathode or a stack structure of anode/hole transport
layer/organic emission layer/electron transport layer/cathode.
SUMMARY
[0006] The present invention also provides an organic
light-emitting device including the heterocyclic compound.
[0007] The present invention also provides a flat panel display
device including the organic light-emitting device.
[0008] According to an aspect of the present invention, there is
provided a heterocyclic compound represented by Formula 1
below:
##STR00002##
[0009] wherein R.sub.1 to R.sub.5 are each independently selected
from the group consisting of a hydrogen atom, a heavy hydrogen
atom, a substituted or unsubstituted C1-C60 alkyl group, a
substituted or unsubstituted C2-C60 alkenyl group, a substituted or
unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted
C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60
alkoxy group, a substituted or unsubstituted C5-C60 aryloxy group,
a substituted or unsubstituted C5-C60 arylthio group, a substituted
or unsubstituted C5-C60 aryl group, an amino group substituted with
a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or
unsubstituted C3-C60 heteroaryl group, a substituted or
unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a
cyano group, a nitro group, a hydroxy group, and a carboxy
group.
[0010] According to another aspect of the present invention, there
is provided a heterocyclic compound represented by Formula 2
below:
##STR00003##
[0011] wherein R.sub.6 to R.sub.10 are each independently selected
from the group consisting of a hydrogen atom, a heavy hydrogen
atom, a substituted or unsubstituted C1-C60 alkyl group, a
substituted or unsubstituted C2-C60 alkenyl group, a substituted or
unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted
C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60
alkoxy group, a substituted or unsubstituted C5-C60 aryloxy group,
a substituted or unsubstituted C5-C60 arylthio group, a substituted
or unsubstituted C5-C60 aryl group, an amino group substituted with
a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or
unsubstituted C3-C60 heteroaryl group, a substituted or
unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a
cyano group, a nitro group, a hydroxy group, and a carboxy
group.
[0012] R.sub.1 to R.sub.10 may be each independently selected from
the group consisting of a hydrogen atom, a heavy hydrogen atom, a
cyano group, a halogen atom, a substituted or unsubstituted C1-C20
alkyl group, a substituted or unsubstituted C5-C40 aryl group, a
substituted or unsubstituted C3-C40 heteroaryl group, an amino
group substituted with a C5-C40 aryl group or a C3-C20 heteroaryl
group, and a substituted or unsubstituted C6-C40 condensed
polycyclic group.
[0013] R.sub.1 to R.sub.10 may be each independently selected from
the group consisting of a hydrogen atom, a heavy hydrogen atom, a
halogen atom, a cyano group, a C1-C20 alkyl group, and compounds
represented by Formulae 2a to 2g below:
##STR00004##
wherein Q.sub.1 is selected from the group consisting of linking
groups represented by --C(R.sub.11)(R.sub.12)--, --N(R.sub.13)--,
--S--, and --O--;
[0014] Y.sub.1, Y.sub.2, and Y.sub.3 are each independently
selected from the group consisting of linking groups represented by
--N.dbd. and --C(R.sub.14).dbd.;
[0015] Z.sub.1, Z.sub.2, Ar.sub.12, Ar.sub.13, R.sub.11, R.sub.12,
and R.sub.13 are each independently selected from the group
consisting of a hydrogen atom, a heavy hydrogen atom, a substituted
or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0016] Ar.sub.11 is selected from the group consisting of a
substituted or unsubstituted C1-C20 alkylene group, a substituted
or unsubstituted C5-C20 arylene group, and a substituted or
unsubstituted C3-C20 heteroarylene group;
[0017] p is an integer from 1 to 12;
[0018] r is an integer from 0 to 5; and
[0019] * is a binding site.
[0020] R.sub.1 to R.sub.10 may be each independently selected from
the group consisting of a hydrogen atom, a heavy hydrogen atom, a
halogen atom, a cyano group, a methyl group, an ethyl group, a
propyl group, a butyl group, a pentyl group, and compounds
represented by Formulae 3a to 3d below:
##STR00005##
[0021] wherein Z.sub.1 is selected from the group consisting of a
hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0022] p is an integer from 1 to 12; and
[0023] * is a binding site.
[0024] R.sub.1, R.sub.2, R.sub.6, and R.sub.7 may be each
independently selected from the group consisting of a hydrogen
atom, a heavy hydrogen atom, a substituted or unsubstituted C1-C20
alkyl group, a substituted or unsubstituted C5-C20 aryl group, and
R.sub.3, R.sub.4, R.sub.5, R.sub.8, R.sub.9, and R.sub.10 are each
independently selected from the group consisting of a hydrogen
atom, a heavy hydrogen atom, a halogen atom, a cyano group, a
C1-C20 alkyl group, and compounds represented by Formulae 2a to 2g
below:
##STR00006##
[0025] wherein Q.sub.1 is selected from the group consisting of
linking groups represented by --C(R.sub.11)(R.sub.12)--,
--N(R.sub.13)--, --S--, and --O--;
[0026] Y.sub.1, Y.sub.2, and Y.sub.3 are each independently
selected from the group consisting of linking groups represented by
--N.dbd. and --C(R.sub.14).dbd.;
[0027] Z.sub.1, Z.sub.2, Ar.sub.12, Ar.sub.13, R.sub.11, R.sub.12,
and R.sub.13 are each independently selected from the group
consisting of a hydrogen atom, a heavy hydrogen atom, a substituted
or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0028] Ar.sub.11 is selected from the group consisting of a
substituted or unsubstituted C1-C20 alkylene group, a substituted
or unsubstituted C5-C20 arylene group, and a substituted or
unsubstituted C3-C20 heteroarylene group;
[0029] p is an integer from 1 to 12; and
[0030] r is an integer from 0 to 5; and
[0031] * is a binding site.
[0032] R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7,
R.sub.9, and R.sub.10 may be each independently selected from the
group consisting of a hydrogen atom, a heavy hydrogen atom, a
substituted or unsubstituted C1-C20 alkyl group, and a substituted
or unsubstituted C5-C20 aryl group, and R.sub.3 and R.sub.8 are
each independently selected from the group consisting of a hydrogen
atom, a heavy hydrogen atom, a halogen atom, a cyano group, a
methyl group, an ethyl group, a propyl group, a butyl group, a
pentyl group, and compounds represented by Formulae 3a to 3d
below:
##STR00007##
[0033] wherein Z.sub.1 is selected from the group consisting of a
hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0034] p is an integer from 1 to 12; and
[0035] * is a binding site.
[0036] R.sub.1, R.sub.2, R.sub.6, and R.sub.7 may be each
independently a methyl group or a phenyl group, and R.sub.3,
R.sub.4, R.sub.5, R.sub.8, R.sub.9, and R.sub.10 are each
independently selected from the group consisting of a hydrogen
atom, a heavy hydrogen atom, a halogen atom, a cyano group, a
methyl group, an ethyl group, a propyl group, a butyl group, a
pentyl group, and compounds selected from the group consisting of
Formulae 3a to 3d below:
##STR00008##
[0037] wherein Z.sub.1 is selected from the group consisting of a
hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0038] p is an integer from 1 to 12; and
[0039] * is a binding site.
[0040] The compound represented by Formula 1 may include one of the
compounds below.
##STR00009##
[0041] According to another aspect of the present invention, there
is provided an organic light-emitting device including:
[0042] a first electrode;
[0043] a second electrode; and
[0044] an organic layer interposed between the first electrode and
the second electrode,
[0045] wherein the organic layer includes a heterocyclic compound
represented by Formula 1 or 2.
[0046] The organic layer may include a hole injection layer, a hole
transport layer, a single layer having both hole injecting and
transporting capabilities, an electron injection layer, an electron
transport layer, or a single layer having both electron injecting
and transporting capabilities.
[0047] The organic layer may be an emission layer, wherein the
heterocyclic compound represented by Formula 1 or 2 is used as a
host or a fluorescent dopant for a fluorescent or phosphorescent
device.
[0048] The organic layer may include an emission layer, a hole
transport layer, and an electron transport layer, wherein the
emission layer further includes an anthracene compound, an
arylamine compound, or a styryl compound.
[0049] The organic layer may include an emission layer, a hole
transport layer, and an electron transport layer, wherein one of
the red, green, blue, and white layers of the emission layer
further includes a phosphorescent compound.
[0050] The organic layer may be a blue emission layer.
[0051] The organic layer may be a blue emission layer, wherein the
compound represented by Formula 1 or 2 is used as a blue host.
[0052] The organic layer may include a plurality of layers, wherein
at least one layer of the organic layer is formed by a wet process
using a heterocyclic compound represented by Formula 1 or 2.
[0053] According to another aspect of the present invention, there
is provided a flat panel display device including the organic
light-emitting device, wherein a first electrode of the organic
light-emitting device is electrically connected to a source
electrode or a drain electrode of a thin film transistor.
BRIEF DESCRIPTION OF THE DRAWING
[0054] The embodiments will become apparent by describing in detail
exemplary embodiments thereof with reference to the attached
drawing in which:
[0055] FIG. 1 illustrates an organic light-emitting device
according to an embodiment.
DETAILED DESCRIPTION
[0056] Hereinafter, the present invention will now be described
more fully with reference to the accompanying drawing, in which an
exemplary embodiment of the invention is shown.
[0057] Anthracene derivatives may be used as materials for forming
an organic emission layer. PBD, PF-6P, and PyPySPyPy, as well as
Alq3 may also be used as materials for forming an electron
transport layer. For example, an organic light-emitting device may
be manufactured using a compound of a phenylanthracene dimer or
trimer. However, such organic light-emitting devices may have a
narrow energy gap and low blue-light color purity since two or
three oligomeric species of anthracene may be linked by
conjugation.
[0058] In addition, such compounds may be highly vulnerable to
oxidation and thus may be liable to produce impurities, thereby
necessitating purification. Thus, organic light-emitting devices
may be manufactured using an anthracene compound including
naphthalene substituted for anthracene at 1,9 position or using a
diphenylanthracene compound including an aryl group substituted for
a phenyl group at an m-position. However, these organic
light-emitting devices may have low light-emission efficiency.
[0059] In addition, organic light-emitting devices may be
manufactured using a naphthalene-substituted monoanthracene
derivative. However, the compound may have a low light-emission
efficiency of about 1 cd/A, and thus, such organic light-emitting
devices may not be suitable for practical use. Organic
light-emitting devices may also be manufactured using compounds
having a phenylanthracene structure. However, these compounds may
be substituted with an aryl group at an m-position, and thereby may
have a low light-emission efficiency of about 2 cd/A in spite of
excellent thermal resistance.
[0060] According to an embodiment, a heterocyclic compound
represented by Formula 1 or Formula 2, below, is provided.
##STR00010##
[0061] In Formula 1, R.sub.1 to R.sub.5 may each independently be
selected from the group of a hydrogen atom, a heavy hydrogen atom,
a substituted or unsubstituted C1-C60 alkyl group, a substituted or
unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted
C2-C60 alkynyl group, a substituted or unsubstituted C3-C60
cycloalkyl group, a substituted or unsubstituted C1-C60 alkoxy
group, a substituted or unsubstituted C5-C60 aryloxy group, a
substituted or unsubstituted C5-C60 arylthio group, a substituted
or unsubstituted C5-C60 aryl group, an amino group substituted with
a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or
unsubstituted C3-C60 heteroaryl group, a substituted or
unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a
cyano group, a nitro group, a hydroxy group, and a carboxy
group.
##STR00011##
[0062] In Formula 2, R.sub.6 to R.sub.10 may each independently be
selected from the group of a hydrogen atom, a heavy hydrogen atom,
a substituted or unsubstituted C1-C60 alkyl group, a substituted or
unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted
C2-C60 alkynyl group, a substituted or unsubstituted C3-C60
cycloalkyl group, a substituted or unsubstituted C1-C60 alkoxy
group, a substituted or unsubstituted C5-C60 aryloxy group, a
substituted or unsubstituted C5-C60 arylthio group, a substituted
or unsubstituted C5-C60 aryl group, an amino group substituted with
a C5-C60 aryl group or a C3-C60 heteroaryl group, a substituted or
unsubstituted C3-C60 heteroaryl group, a substituted or
unsubstituted C6-C60 condensed polycyclic group, a halogen atom, a
cyano group, a nitro group, a hydroxy group, and a carboxy
group.
[0063] The heterocyclic compounds of Formulae 1 and 2 may be
suitable as a material for forming an emission layer, an electron
transport layer, or an electron injection layer of an organic
light-emitting device. The heterocyclic compounds of Formulae 1 and
2 having a heterocyclic group therein may have a high glass
transition temperature (Tg) or a high melting point due to
inclusion of the heterocyclic group. Thus, the heterocyclic
compound may have high thermal resistance against Joule heat
generated in an organic layer, between organic layers, or between
an organic layer and a metallic electrode when light emission
occurs, and may have high durability in a high-temperature
environment.
[0064] An organic light-emitting device manufactured using the
compound of Formula 1 or 2 may have high durability when stored or
operated.
[0065] Substituents in the compounds of Formulae 1 and 2 will now
be described in detail.
[0066] In an implementation, in Formulae 1 and 2, R.sub.1 to
R.sub.10 may each independently be selected from the group of a
hydrogen atom, a heavy hydrogen atom, a cyano group, a halogen
atom, a substituted or unsubstituted C1-C20 alkyl group, a
substituted or unsubstituted C5-C40 aryl group, a substituted or
unsubstituted C3-C40 heteroaryl group, an amino group substituted
with a C5-C40 aryl group or a C3-C20 heteroaryl group, and a
substituted or unsubstituted C6-C40 condensed polycyclic group.
[0067] In another implementation, in Formulae 1 and 2, R.sub.1 to
R.sub.10 may each independently be selected from the group of a
hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a C1-C20 alkyl group, and compounds represented by Formulae
2a to 2g below.
##STR00012##
[0068] In Formulae 2a to 2g, Q.sub.1 may be selected from the group
of linking groups represented by --C(R.sub.11)(R.sub.12)--,
--N(R.sub.13)--, --S--, and --O--;
[0069] Y.sub.1, Y.sub.2, and Y.sub.3 may each independently be
selected from the group of linking groups represented by --N.dbd.
and --C(R.sub.14).dbd.;
[0070] Z.sub.1, Z.sub.2, Ar.sub.12, Ar.sub.13, R.sub.11, R.sub.12,
and R.sub.13 may each independently be selected from the group of a
hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0071] Ar.sub.11 may be selected from the group of a substituted or
unsubstituted C1-C20 alkylene group, a substituted or unsubstituted
C5-C20 arylene group, and a substituted or unsubstituted C3-C20
heteroarylene group;
[0072] p may be an integer from 1 to 12; r may be an integer from 0
to 5; and * may be a binding site.
[0073] In another implementation, in Formulae 1 and 2, R.sub.1 to
R.sub.10 may each independently be selected from the group of a
hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a methyl group, an ethyl group, a propyl group, a butyl
group, a pentyl group, and compounds represented by Formulae 3a to
3d below.
##STR00013##
[0074] In Formulae 3a to 3d, Z.sub.1 may be selected from the group
of a hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0075] p may be an integer from 1 to 12; and * may be a binding
site.
[0076] In yet another implementation, in Formulae 1 and 2, R.sub.1,
R.sub.2, R.sub.6, and R.sub.7 may each independently be selected
from the group of a hydrogen atom, a heavy hydrogen atom, a
substituted or unsubstituted C1-C20 alkyl group, a substituted or
unsubstituted C5-C20 aryl group, and R.sub.3, R.sub.4, R.sub.5,
R.sub.8, R.sub.9, and R.sub.10 are each independently selected from
the group consisting of a hydrogen atom, a heavy hydrogen atom, a
halogen atom, a cyano group, a C1-C20 alkyl group, and compounds
represented by Formulae 2a to 2g below.
##STR00014##
[0077] In Formulae 2a to 2g, Q.sub.1 may be selected from the group
of linking groups represented by --C(R.sub.11)(R.sub.12)--,
--N(R.sub.13)--, --S--, and --O--;
[0078] Y.sub.1, Y.sub.2, and Y.sub.3 may each independently be
selected from the group of linking groups represented by --N.dbd.
and --C(R.sub.14).dbd.;
[0079] Z.sub.1, Z.sub.2, Ar.sub.12, Ar.sub.13, R.sub.11, R.sub.12,
and R.sub.13 may each independently be selected from the group of a
hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0080] Ar.sub.11 may be selected from the group of a substituted or
unsubstituted C1-C20 alkylene group, a substituted or unsubstituted
C5-C20 arylene group, and a substituted or unsubstituted C3-C20
heteroarylene group;
[0081] p may be an integer from 1 to 12; r may be an integer from 0
to 5; and * may be a binding site.
[0082] In still another implementation, in Formulae 1 and 2,
R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.9, and
R.sub.10 may each independently be selected from the group of a
hydrogen atom, a heavy hydrogen atom, a C1-C20 alkyl group, and a
substituted or unsubstituted C5-C20 aryl group, and R.sub.3 and
R.sub.8 are each independently selected from the group consisting
of a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano
group, a methyl group, an ethyl group, a propyl group, a butyl
group, a pentyl group, and compounds represented by Formulae 3a to
3d below.
##STR00015##
[0083] In Formulae 3a to 3d, Z.sub.1 may be selected from the group
of a hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0084] p may be an integer from 1 to 12; and * may be a binding
site.
[0085] In still another implementation, in Formulae 1 and 2,
R.sub.1, R.sub.2, R.sub.6, and R.sub.7 may each independently be a
methyl group or a phenyl group, and R.sub.3, R.sub.4, R.sub.5,
R.sub.8, R.sub.9, and R.sub.10 may each independently be selected
from the group of a hydrogen atom, a heavy hydrogen atom, a halogen
atom, a cyano group, a methyl group, an ethyl group, a propyl
group, a butyl group, a pentyl group, and compounds selected from
the group consisting of Formulae 3a to 3d below.
##STR00016##
[0086] In Formulae 3a to 3d, Z.sub.1 may be selected from the group
of a hydrogen atom, a heavy hydrogen atom, a substituted or
unsubstituted C1-C20 alkyl group, a substituted or unsubstituted
C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl
group, a substituted or unsubstituted C6-C20 condensed polycyclic
group, a halogen atom, a cyano group, a nitro group, a hydroxy
group, and a carboxy group;
[0087] p may be an integer from 1 to 12; and * may be a binding
site.
[0088] Hereinafter, substituents described with reference to
Formulae 1 and 2 will now be described in detail. In this regard,
the number of carbon atoms in substituents is presented only for
illustrative purposes and does not limit the characteristics of the
substituents.
[0089] The C1-C60 alkyl group used herein may be linear or
branched. Examples of the alkyl group may include, but are not
limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl,
iso-amyl, hexyl, heptyl, octyl, nonyl, and dodecyl. At least one
hydrogen atom of the alkyl group may be substituted with a heavy
hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a
cyano group, an amino group, an amidino group, hydrazine,
hydrazone, a carboxyl group or a salt thereof, a sulfonic acid
group or a salt thereof, a phosphoric acid group or a salt thereof,
a C1-C10 alkyl group, a C1-C10 alkoxy group, a C2-C10 alkenyl
group, a C2-C10 alkynyl group, a C6-C16 aryl group, or a C4-C16
heteroaryl group.
[0090] The C2-C60 alkenyl group used herein may refer to a
hydrocarbon chain having at least one carbon-carbon double bond at
a center or at a terminal of the unsubstituted alkyl group.
Examples of the C2-C60 alkenyl group may include ethenyl, propenyl,
and butenyl. At least one hydrogen atom of the alkenyl group may be
substituted with the same substituent groups as described above in
connection with the alkyl group.
[0091] The C2-C60 alkynyl group used herein may refer to a
hydrocarbon chain having at least one carbon-carbon triple bond at
a center or at a terminal of the alkyl group. Examples of the
C2-C60 alkynyl group may include acetylene, propylene,
phenylacetylene, naphthylacetylene, isopropylacetylene,
t-butylacetylene, and diphenylacetylene. At least one hydrogen atom
of the alkynyl group may be substituted with the same substituent
groups as described above in connection with the alkyl group.
[0092] The C3-C60 cycloalkyl group used herein may refer to a
C3-C60 cyclic alkyl group wherein at least one hydrogen atom in the
cycloalkyl group may be substituted with the same substituent group
described above in connection with the C1-C60 alkyl group.
[0093] The C1-C60 alkoxy group used herein may be a group having a
structure of --OA wherein A is a C1-C60 alkyl group as described
above. Examples of the C1-C60 alkoxy group may include methoxy,
ethoxy, propoxy, isopropyloxy, butoxy, and pentoxy. At least one
hydrogen atom of the alkoxy group may be substituted with the same
substituent groups as described above in connection with the alkyl
group.
[0094] The C5-C60 aryl group used herein may refer to a carbocyclic
aromatic system containing at least one ring. At least two rings
may be fused to each other or linked to each other by a single
bond. The term `aryl` may refer to an aromatic system, such as
phenyl, naphthyl, or anthracenyl. At least one hydrogen atom in the
aryl group may be substituted with the same substituent groups
described with reference to the C1-C60 alkyl group.
[0095] Examples of the substituted or unsubstituted C5-C60 aryl
group may include a phenyl group, a C1-C10 alkylphenyl group (for
example, ethylphenyl group), a halophenyl group (for example, o-,
m-, and p-fluorophenyl group, dichlorophenyl group), a cyanophenyl
group, dicyanophenyl group, a trifluoromethoxyphenyl group, a
biphenyl group, a halobiphenyl group, a cyanobiphenyl group, a
C1-C10 alkyl biphenyl group, a C1-C10 alkoxybiphenyl group, o-, m-,
and p-tolyl groups, o-, m-, and p-cumenyl groups, a mesityl group,
a phenoxyphenyl group, a (.alpha.,.alpha.-dimethylbenzene)phenyl
group, a (N,N'-dimethyl)aminophenyl group, a
(N,N'-diphenyl)aminophenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, a halonaphthyl group (for example,
fluoronaphthyl group), a C1-C10 alkylnaphthyl group (for example,
methylnaphthyl group), a C1-C10 alkoxynaphthyl group (for example,
methoxynaphthyl group), a cyanonaphthyl group, an anthracenyl
group, an azulenyl group, a heptalenyl group, an acenaphthylenyl
group, a phenalenyl group, a fluorenyl group, an anthraquinolyl
group, a methylanthryl group, a phenanthryl group, a triphenylene
group, a pyrenyl group, a chrycenyl group, an ethyl-chrysenyl
group, a picenyl group, a perylenyl group, a chloroperylenyl group,
a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a
hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronelyl
group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl
group, a pyranthrenyl group, and an ovalenyl group.
[0096] The C4-C60 heteroaryl group used herein may include one,
two, or three hetero atoms selected from the group of N, O, P, and
S. At least two rings may be fused to each other or linked to each
other by a single bond. Examples of the C4-C60 heteroaryl group may
include a pyrazolyl group, an imidazolyl group, an oxazolyl group,
a thiazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a
pyrimidinyl group, a triazinyl group, a carbazolyl group, an
indolyl group, a quinolinyl group, an isoquinolinyl group, and a
dibenzothiophene group. In addition, at least one hydrogen atom in
the heteroaryl group may be substituted with the same substituent
groups described above with reference to the C1-C60 alkyl
group.
[0097] The C5-C60 aryloxy group used herein may refer to a group
represented by --OA.sub.1, wherein A.sub.1 is a C5-C60 aryl group.
An example of the aryloxy group may include a phenoxy group. At
least one hydrogen atom in the aryloxy group may be substituted
with the same substituent groups described with reference to the
C1-C60 alkyl group.
[0098] The C5-C60 arylthio group used herein may refer to a group
represented by --SA.sub.1, wherein A.sub.1 is a C5-C60 aryl group.
Examples of the arylthio group may include a benzenethio group and
a naphthylthio group. At least one hydrogen atom in the arylthio
group may be substituted with the substituent groups described with
reference to the C1-C60 alkyl group.
[0099] The C6-C60 condensed polycyclic group may be a substituent
including at lest two rings wherein at least one aromatic ring
and/or at least one non-aromatic ring are fused to each other.
[0100] Examples of the compound represented by Formula 1 or 2 may
include compounds represented by the following Compounds 1 through
57. However, the compound represented by Formula 1 or 2 is not
limited thereto.
##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021##
##STR00022## ##STR00023## ##STR00024## ##STR00025##
[0101] An organic light-emitting device according to an embodiment
may include a first electrode, a second electrode, and an organic
layer interposed between the first electrode and the second
electrode. The organic layer may include the heterocyclic compound
represented by Formula 1 or 2 described above.
[0102] The organic layer including the heterocyclic compound
represented by Formula 1 or 2 may include a hole injection layer
(HIL), a hole transport layer (HTL), a single layer having both
hole injecting and hole transporting capabilities, an electron
injection layer (EIL), an electron transport layer (ETL), or a
single layer having both electron injecting and electron
transporting capabilities.
[0103] Alternatively, the organic layer including the heterocyclic
compound represented by Formula 1 or 2 may be an emission layer
(EML); and the heterocyclic compound represented by Formula 1 or 2
may be used as a host or a dopant for a fluorescent or
phosphorescent device.
[0104] According to the present embodiment, the organic layer of
the organic light-emitting device may include an EML, an HTL, and
an ETL. If the EML, the HTL, or the ETL includes the compound of
Formula 1 or 2, the EML may include an anthracene compound, an
arylamine compound, or a styryl compound.
[0105] At least one hydrogen atom of the anthracene compound, the
arylamine compound, or the styryl compound may be substituted with
the same substituent groups described above with reference to the
C1-C60 alkyl group. The arylamine may refer to a C5-C60 arylamine
group.
[0106] If the organic layer of the organic light-emitting device
according to the present embodiment includes the EML, the HTL, and
the ETL, and the EML, the HTL, or the ETL includes the compound of
Formula 1 or 2, a red, green, blue, or white layer of the EML may
include a phosphorescent compound.
[0107] The organic layer of the organic light-emitting device may
be a blue EML. If the organic layer of the organic light-emitting
device is a blue EML, the compound of Formula 1 or 2 may be used as
a blue host.
[0108] The first electrode may be an anode; and the second
electrode may be a cathode, but the reverse is also possible.
[0109] For example, the organic light-emitting device according to
the present embodiment may have a structure of first
electrode/HIL/EML/second electrode, a structure of first
electrode/HIL/HTL/EML/ETL/second electrode, or a structure of first
electrode/HIL/HTL/EML/ETL/EIL/second electrode. An organic
light-emitting device may also have a structure of first
electrode/single layer having both hole injecting and hole
transporting capabilities/EML/ETL/second electrode, or a structure
of first electrode/single layer having both hole injecting and hole
transporting capabilities/EML/ETL/EIL/second electrode. The organic
light-emitting device may also have a structure of first
electrode/HTL/EML/single layer having both electron injecting and
electron transporting capabilities/second electrode, a structure of
first electrode/HIL/EML/single layer having both electron injecting
and electron transporting capabilities/second electrode, or a
structure of first electrode/HIL/HTL/EML/single layer having both
electron injecting and electron transporting capabilities/second
electrode.
[0110] The organic light-emitting device according to the present
embodiment may be a top-emission type organic light-emitting device
or a bottom-emission type organic light-emitting device.
[0111] Hereinafter, a method of manufacturing an organic
light-emitting device, according to an embodiment will be described
with reference to FIG. 1. Referring to FIG. 1, the organic
light-emitting device may include a substrate, a first electrode
(anode), a HIL, a HTL, an EML, an ETL, an EIL, and a second
electrode (cathode).
[0112] First, the first electrode may be formed by depositing or
sputtering a material for forming the first electrode having a high
work function on a substrate. The first electrode may constitute an
anode or a cathode. The substrate may be any substrate commonly
used in organic light-emitting devices, and may be, for example, a
glass substrate or a transparent plastic substrate with excellent
mechanical strength, thermal stability, transparency, surface
smoothness, ease of handling, and water resistance. The material
for forming the first electrode may be indium tin oxide (ITO),
indium zinc oxide (IZO), tin oxide (SnO.sub.2), zinc oxide (ZnO),
aluminum (Al), silver (Ag), magnesium (Mg), or the like, which has
excellent conductivity, and may form a transparent or reflective
electrode.
[0113] Then, a HIL may be formed on the first electrode by vacuum
deposition, spin coating, casting, Langmuir Blodgett (LB)
deposition, or the like.
[0114] When the HIL is formed using vacuum deposition, the
deposition conditions may vary according to a compound that is used
to form the HIL, and the structure and thermal characteristics of
the HIL to be formed. For example, the deposition conditions may
include a deposition temperature of 100 to 500.degree. C., a vacuum
pressure of 10.sup.-8 to 10.sup.-3 torr, and a deposition rate of
0.01 to 100 .ANG./sec.
[0115] When the HIL is formed using spin coating, coating
conditions may vary according to a compound that is used to form
the HIL, and the structure and thermal properties of the HIL to be
formed. For example, the coating conditions may include a coating
speed of about 2000 rpm to about 5000 rpm, and a thermal treatment
temperature of about 80.degree. C. to about 200.degree. C., wherein
the thermal treatment is for removing a solvent after coating.
[0116] The HIL may be formed of any material that is commonly used
to form a HIL. Examples of the material may include a
phthalocyanine compound such as copper phthalocyanine,
4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA),
N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), TDATA, 2T-NATA,
polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),
poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)
(PEDOT/PSS), polyaniline/camphor sulfonicacid (Pani/CSA), and
(polyaniline)/poly(4-styrenesulfonate (PANI/PSS), but are not
limited thereto.
##STR00026##
[0117] A thickness of the HIL may be about 100 to 10,000 .ANG.,
e.g., 100 to 1,000 .ANG.. When the HIL has a thickness within the
above range, the HIL may have excellent hole injecting
characteristics without an increase in driving voltage.
[0118] Then, the HTL may be formed on the HIL using various
methods, for example by vacuum deposition, spin coating, casting,
and LB deposition. When the HTL is formed using vacuum deposition
or spin coating, the deposition or coating conditions may be
similar to those applied to form the HIL, although the deposition
or coating conditions may vary according to a material used to form
the HTL.
[0119] The material for forming the HTL may include the
heterocyclic compound of Formula 1 or 2 or any known hole
transporting material. Examples of such hole transporting materials
may include, but are not limited to, carbazole derivatives such as
N-phenylcarbazole or polyvinylcarbazole, and amine derivatives
having an aromatic condensed ring, such as NPB,
N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine
(TPD), or the like.
##STR00027##
[0120] The HTL may have a thickness of about 50 .ANG. to about
1,000 .ANG., e.g., about 100 .ANG. to about 600 .ANG.. When the HTL
has a thickness within the above range, the HTL may have excellent
hole transporting characteristics without a substantial increase in
driving voltage.
[0121] Then, the EML may be formed on the HTL using various
methods, for example, vacuum deposition, spin coating, casting, and
LB deposition. When the EML is formed using vacuum deposition or
spin coating, the deposition or coating conditions may be similar
to those applied to form the HIL, although the deposition and
coating conditions may vary according to a material that is used to
form the EML.
[0122] The EML may include the heterocyclic compound of Formula 1
or 2 described above. For example, the heterocyclic compound of
Formula 1 or 2 may be used as a host or a dopant. The EML may be
formed using a variety of well-known light-emitting materials, in
addition to the heterocyclic compound of Formula 1 or 2. The EML
may also be formed using a well-known host and dopant. The dopant
for forming the EML may include either a fluorescent dopant or a
phosphorescent dopant, which are widely known in the art.
[0123] Examples of the host may include Alq3,
4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK),
9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA,
1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),
3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), E3, and
distyrylarylene (DSA), but are not limited thereto.
##STR00028##
[0124] Examples of red dopants may include platinum(II)
octaethylporphyrin (PtOEP), Ir(piq).sub.3, Btp.sub.2Ir(acac), and
DCJTB, but are not limited thereto.
##STR00029##
[0125] Examples of green dopants may include Ir(ppy).sub.3 (where
"ppy" denotes phenylpyridine), Ir(ppy).sub.2(acac), Ir(mpyp).sub.3,
and C545T, but are not limited thereto.
##STR00030##
[0126] Examples of the blue dopant may include the heterocyclic
compound represented by Formula 1 or 2. Alternatively, examples of
well-known blue dopants include F.sub.2Irpic,
(F.sub.2ppy).sub.2Ir(tmd), Ir(dfppz).sub.3, ter-fluorene,
4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi), and
2,5,8,11-tetra-t-butyl pherylene (TBPe), but are not limited
thereto.
##STR00031##
[0127] An amount of the dopant may be in a range of about 0.1 to
about 20 parts by weight, or about 0.5 to about 12 parts by weight,
based on 100 parts by weight of the EML material (which is
equivalent to the total weight of the host and the dopant). When
the amount of the dopant is within the above range, concentration
quenching may be substantially prevented.
[0128] The EML may have a thickness of about 100 .ANG. to about
1,000 .ANG., e.g., about 200 .ANG. to about 600 .ANG.. When the EML
has a thickness within the above range, the EML may have excellent
light-emitting characteristics without a substantial increase in
driving voltage.
[0129] When the EML includes a phosphorescent dopant, a hole
blocking layer (HBL) (not shown in FIG. 1) may be formed on the EML
in order to prevent diffusion of triplet excitons or holes into the
ETL. In this case, the HBL may be formed of any material that is
commonly used to form a HBL, without limitation. Examples of such
HBL materials may include oxadiazole derivatives, triazole
derivatives, phenathroline derivatives, Balq, and BCP.
[0130] The HBL may have a thickness of about 50 .ANG. to about
1,000 .ANG., e.g., about 100 .ANG. to about 300 .ANG.. When the
thickness of the HBL is within the range described above, the HBL
may have excellent hole blocking characteristics without a
substantial increase in driving voltage.
[0131] Then, the ETL may be formed on the EML (or HBL) using
various methods, for example, by vacuum deposition, spin coating,
casting, or the like. When the ETL is formed using vacuum
deposition or spin coating, the deposition or coating conditions
may be similar to those applied to form the HIL, although the
deposition and coating conditions may vary according to the
material that is used to form the ETL.
[0132] The electron transporting material may include the
heterocyclic compound of Formula 1 or 2 described above.
Alternatively, the ETL may be formed of any material that is widely
known in the art. Examples of electron transporting materials may
include quinoline derivatives, such as
tris(8-quinolinolate)aluminum (Alq3), TAZ, or Balq, but are not
limited thereto.
##STR00032##
[0133] The ETL may have a thickness of about 100 .ANG. to about
1,000 .ANG., e.g., about 100 .ANG. to about 500 .ANG.. When the ETL
has a thickness within the above range, the ETL may have excellent
electron transporting characteristics without a substantial
increase in driving voltage.
[0134] In addition, the EIL, which may facilitate injection of
electrons from the cathode, may be formed on the ETL.
[0135] Alternatively, materials, such as LiF, NaCl, CsF, Li.sub.2O,
or BaO, may be used to form the EIL. The deposition or coating
conditions for forming the EIL may be similar to those applied to
form the HIL, although the deposition and coating conditions may
vary according to the material that is used to form the EIL.
[0136] The EIL may have a thickness of about 1 .ANG. to 100 .ANG.,
e.g., about 5 .ANG. to about 90 .ANG.. When the EIL has a thickness
within the above range, the EIL may have excellent electron
injecting characteristics without a substantial increase in driving
voltage.
[0137] Finally, the second electrode may be formed on the EIL
using, for example, vacuum deposition, sputtering, or the like. The
second electrode may constitute a cathode or an anode. The material
for forming the second electrode may include a metal, an alloy, or
an electrically conductive compound, materials which have a low
work function, or a mixture thereof. In an implementation, the
second electrode may be formed of lithium (Li), magnesium (Mg),
aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), magnesium
(Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like. In
addition, in order to manufacture a top-emission type organic
light-emitting device, a transparent cathode formed of a
transparent material such as ITO or IZO may be used as the second
electrode.
[0138] The organic light-emitting device according to the present
embodiment may be included in various types of flat panel display
devices, such as a passive matrix organic light-emitting display
device or an active matrix organic light-emitting display device.
In particular, when the organic light-emitting device is included
in an active matrix organic light-emitting display device including
a thin-film transistor, the first electrode formed on the substrate
may function as a pixel electrode, electrically connected to a
source electrode or a drain electrode of the thin-film transistor.
Moreover, the organic light-emitting device may also be included in
a flat panel display device having a double-sided screen.
[0139] If the organic light-emitting device according to the
present embodiment includes a plurality of organic layers, at least
one of the organic layers may be formed of the heterocyclic
compound of Formula 1 or 2 by using a deposition process or a wet
process of coating a solution of the heterocyclic compound of
Formula 1 or 2.
[0140] Hereinafter, the present invention will be described in
detail with reference to synthesis examples of Compounds 2, 16, 21,
24, 25, and 45 and other examples. However, it will be understood
that the embodiments are not limited to the particular details
described. Further, the Comparative Examples are set forth to
highlight certain characteristics of certain embodiments, and are
not to be construed as either limiting the scope of the invention
as exemplified in the Examples or as necessarily being outside the
scope of the invention in every respect.
EXAMPLES
Synthesis Example 1
Synthesis of Compound 2
##STR00033##
[0141] Synthesis of Intermediate I-1
[0142] 5.2 g (20 mmol) of 2-amino-7-bromofluorene and 0.18 g (1
mmol) of triethylbenzylammonium salt were dissolved in 50 mL of a
mixture of DMSO and a 50% sodium hydroxide solution (1:1). 6.25 g
(44 mmol) of methyl iodide was added thereto, and the mixture was
stirred for 10 hours. 50 mL of water was added thereto, and the
mixture was subjected to extraction three times with 50 mL of ethyl
ether. An organic layer was collected and dried using magnesium
sulfate to evaporate the solvent. The residue was separately
purified using silica gel column chromatography to obtain 4.84 g of
Intermediate I-1 (Yield: 84%). The produced compound was identified
using LC-MS. C.sub.15H.sub.14BrN:M.sup.+ 398.19
Synthesis of Intermediate I-2
[0143] 5.76 g (20 mmol) of Intermediate I-1, 3.56 g (18 mmol) of
4-biphenyl borate, and 1.156 g (1 mmol) of Pd(PPH.sub.3).sub.4 were
dissolved in 100 mL of a toluene/2M sodium carbonate solution
(4:1). The mixture was stirred at 100.degree. C. for 12 hours. The
mixture was cooled to room temperature and subjected to extraction
three times with 100 mL of water and 100 mL of diethyl ether. An
organic layer was collected and dried using magnesium sulfate to
evaporate the solvent. The residue was separately purified using
silica gel column chromatography to obtain 5.13 g of Intermediate
I-2 (Yield: 79%). The produced compound was identified using LC-MS.
C27H.sub.23N:M.sup.+ 362.19
Synthesis of Compound 2
[0144] 5 g (13.8 mmol) of Intermediate I-2 and 10 g of a 70%
sulfuric acid solution were added to 4 g of nitrobenzene. The
mixture was heated to 110.degree. C., and 10 g of glycerol, as an
oxidant, was added thereto in drops. Then, the mixture was stirred
at 110.degree. C. for 10 hours. The mixture was cooled to room
temperature and subjected to extraction three times with 50 mL of
water and 50 mL of diethyl ether. An organic layer was collected
and dried using magnesium sulfate to evaporate the solvent. The
residue was separately purified using silica gel column
chromatography to obtain 3.4 g of Compound 2 (Yield: 62%). The
produced compound was identified using LC-MS and NMR.
C.sub.30H.sub.23N.sub.1:M.sup.+ 398.19
[0145] .sup.1H NMR (CDCl.sub.3, 400 MHz) .delta. (ppm) 8.78 (d,
1H), 8.07-7.20 (m, 16H), 1.67 (s, 6H)
Synthesis Example 2
Synthesis of Compound 16
##STR00034##
[0146] Synthesis of Intermediate I-3
[0147] 5.35 g of Intermediate I-3 was synthesized with a yield of
82% in the same manner as the synthesis of Intermediate I-2, using
4-(4-bromophennyl)-pyridine borate and Intermediate I-1. The
produced compound was identified using LC-MS.
C.sub.26H.sub.22N.sub.2:M.sup.+ 363.18
Synthesis of Compound 16
[0148] 3.69 g of Compound 16 was synthesized with a yield of 67% in
the same manner as the synthesis of Compound 2, using Intermediate
1-3, sulfuric acid, nitrobenzene, and glycerol. The produced
compound was identified using LC-MS and NMR.
C.sub.28H.sub.21N.sub.3:M.sup.+ 400.18
[0149] .sup.1H NMR (CDCl.sub.3, 400 MHz) .delta. (ppm) 8.78 (d,
1H), 8.76 (s, 1H), 8.66 (d, 2H), 8.02-7.26 (m, 11H), 1.67 (s,
6H)
Synthesis Example 3
Synthesis of Compound 21
##STR00035##
[0150] Synthesis of Intermediate I-4
[0151] 5.34 g of Intermediate I-4 was synthesized with a yield of
74% in the same manner as the synthesis of Intermediate I-2 using
2-bromo-9,9-dimethyl borate and Intermediate I-1. The produced
compound was identified using LC-MS.
C.sub.30H.sub.27N.sub.1:M.sup.+ 402.22
Synthesis of Compound 21
[0152] 3.62 g of Compound 21 was synthesized with a yield of 60% in
the same manner as the synthesis of Compound 2, using Intermediate
1-4, sulfuric acid, nitrobenzene, and glycerol. The produced
compound was identified using LC-MS and NMR.
C.sub.33H.sub.27N.sub.1:M.sup.+ 438.22
[0153] .sup.1H NMR (CDCl.sub.3, 400 MHz) .delta. (ppm) 8.78 (d,
1H), 8.14-7.26 (m, 14H), 1.67-1.65 (m, 12H)
Synthesis Example 4
Synthesis of Compound 24
##STR00036##
[0154] Synthesis of Intermediate I-5
[0155] 5.20 g of Intermediate I-5 was synthesized with a yield of
72% in the same manner as the synthesis of Intermediate I-2, using
a borate having A-1 structure and Intermediate I-5. The produced
compound was identified using LC-MS.
C.sub.28H.sub.23N.sub.3:M+402.19
Synthesis of Compound 24
[0156] 1.93 g of Compound 24 was synthesized with a yield of 32% in
the same manner as the synthesis of Compound 2, using Intermediate
1-5, sulfuric acid, nitrobenzene, and glycerol. The produced
compound was identified using LC-MS and NMR.
C.sub.31H.sub.23N.sub.1:M.sup.+ 438.19
[0157] .sup.1H NMR (CDCl.sub.3, 400 MHz) .delta. (ppm) 8.78 (d,
1H), 8.09-7.26 (m, 14H), 7.01 (m, 1H), 6.61 (m, 1H), 1.67 (s,
6H)
Synthesis Example 5
Synthesis of Compound 25
##STR00037##
[0158] Synthesis of Intermediate I-6
[0159] 6.88 g of Intermediate I-6 was synthesized with a yield of
80% in the same manner as the synthesis of Intermediate I-2, using
a borate having A-2 structure and Intermediate I-1. The produced
compound was identified using LC-MS. C34H.sub.27N.sub.3:M.sup.+
478.22
Synthesis of Compound 25
[0160] 4.32 g of Compound 25 was synthesized with a yield of 61% in
the same manner as the synthesis of Compound 2, using Intermediate
1-6, sulfuric acid, nitrobenzene, and glycerol. The produced
compound was identified using LC-MS and NMR.
C.sub.37H.sub.27N.sub.3:M.sup.+ 515.23
[0161] .sup.1H NMR (CDCl.sub.3, 400 MHz) .delta. (ppm) 8.78 (d,
1H), 8.11-7.22 (m, 20H), 1.67 (s, 6H)
Synthesis Example 6
Synthesis of Compound 45
##STR00038##
[0162] Synthesis of Intermediate I-7
[0163] 4.95 g of Intermediate I-7 was synthesized with a yield of
83% in the same manner as the synthesis of Intermediate I-2, using
2-naphthyl borate and Intermediate I-1. The produced compound was
identified using LC-MS. C.sub.25H.sub.21N.sub.1:M.sup.+ 336.17
Synthesis of Compound 45
[0164] 1.48 g of Compound 45 was synthesized with a yield of 29% in
the same manner as the synthesis of Compound 2, using Intermediate
1-7, sulfuric acid, nitrobenzene, and glycerol. The produced
compound was identified using LC-MS and NMR.
C.sub.28H.sub.21N.sub.1:M.sup.+ 515.23
[0165] .sup.1H NMR (CDCl.sub.3, 400 MHz) .delta. (ppm) 8.76 (d,
1H), 8.10-7.22 (m, 14H), 1.67 (s, 6H)
Example 1
[0166] An anode was prepared by cutting a Corning 15
.OMEGA./cm.sup.2 (1200 .ANG.) ITO glass substrate to a size of 50
mm.times.50 mm.times.0.7 mm, ultrasonically cleaning the glass
substrate using isopropyl alcohol and pure water for five minutes
each, and then irradiating UV light for 30 minutes and exposing to
ozone to clean. Then, the anode was disposed in a vacuum deposition
apparatus.
[0167] Then, 2-TNATA, which is a known material for forming a HIL,
was vacuum deposited on the glass substrate to form a HIL having a
thickness of 600 .ANG., and then
4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), as a hole
transporting compound, was vacuum deposited on the HIL to form a
HTL having a thickness of 300 .ANG..
##STR00039##
[0168] Then, Compound 2, as a blue fluorescent host, and
1,4-bis(2,2-diphenylvinyl)biphenyl (DPVBi), as a known blue
fluorescent dopant, were deposited simultaneously with a weight
ratio of 98:2, on the HTL, to form an EML having a thickness of 300
.ANG..
[0169] Then, Alq3 was deposited on the EML to form an ETL having a
thickness of 300 .ANG., and then LiF, which is a halogenated alkali
metal, was deposited on the ETL to form an EIL having a thickness
of 10 .ANG.. Then, Al was vacuum deposited on the EIL to form a
cathode having a thickness of 3,000 .ANG., thereby forming a LiF/Al
electrode. As a result, an organic light-emitting device was
manufactured.
Example 2
[0170] An organic light-emitting device was manufactured in the
same manner as in Example 1, except that Compound 45 was used
instead of Compound 2 to form the EML.
Example 3
[0171] An organic light-emitting device was manufactured in the
same manner as in Example 1, except that Compound 21 was used
instead of Compound 2 to form the EML.
Example 4
[0172] An organic light-emitting device was manufactured in the
same manner as in Example 1, except that a known host ADN and a
known dopant DPVBi were used to form the EML and Compound 16 was
used instead of Alq3 to form the ETL on the EML.
Example 5
[0173] An organic light-emitting device was manufactured in the
same manner as in Example 4, except that Compound 24 was used
instead of Compound 16 to form the ETL.
Example 6
[0174] An organic light-emitting device was manufactured in the
same manner as in Example 4, except that Compound 25 was used
instead of Compound 16 to form the ETL.
Example 7
[0175] An organic light-emitting device was manufactured in the
same manner as in Example 1, except that Compound 16 was used
instead of Alq3 to form the ETL.
Example 8
[0176] An organic light-emitting device was manufactured in the
same manner as in Example 7, except that Compound 25 was used
instead of Compound 16 to form the ETL.
Comparative Example 1
[0177] An organic light-emitting device was manufactured in the
same manner as in Example 1, except that a known blue fluorescent
host ADN was used instead of Compound 2 to form the EML.
##STR00040##
[0178] When the compound represented by Formula 1 or 2 according to
an embodiment was used as a host and an electron transporting
material of the organic light-emitting device, driving voltage of
the organic light-emitting device was reduced by 1 V or more than
ADN and Alq3 which are known materials, efficiency was considerably
increased, thereby providing excellent 1-V-L characteristics, and
increasing a lifespan. When the compound according to an embodiment
was used as a host of the organic light-emitting devices prepared
in Examples 1 to 3, driving voltage was reduced by 1 V or more,
efficiency was increased, and lifespan was increased compared to
the organic light-emitting device of Comparative Example 1. In
addition, if the compound according to an embodiment was used as an
electron transporting material in the organic light-emitting
devices prepared in Examples 4 to 6, driving voltage was reduced by
1.3 V or more than that of Comparative Example 1. When the compound
according to an embodiment was used as a host of the EML and an
electron transporting material, driving voltage was reduced by 1.7
V or more, efficiency was increased by about 200%, and lifespan was
increased by 100% or more compared to the organic light-emitting
device of Comparative Example 1. Characteristics and lifespan of
the organic light-emitting devices are shown in Table 1 below.
TABLE-US-00001 TABLE 1 Host or electron Driving Current
transporting voltage density Brightness Efficiency Half-life
material (V) (mA/cm.sup.2) (Cd/A) (Cd/A) Color span (hr @100
mA/cm.sup.2) Example 1 Compound 2 6.25 50 2,335 4.67 blue 192 hr
Example 2 Compound 45 6.17 50 2,415 4.83 blue 208 hr Example 3
Compound 21 6.33 50 2,385 4.77 blue 220 hr Example 4 Compound 16
5.73 50 2,470 4.94 blue 174 hr Example 5 Compound 24 6.06 50 2,571
5.14 blue 191 hr Example 6 Compound 25 5.84 50 2,903 5.80 blue 183
hr Example 7 Compound 2, 5.61 50 3,135 6.27 blue 242 hr Compound 16
Example 8 Compound 2, 5.54 50 3,205 6.41 blue 261 hr Compound 25
Comparative ADN 7.35 50 1,574 3.14 blue 120 hr Example 1
[0179] The heterocyclic compounds according to the embodiments may
exhibit excellent light-emitting characteristics and excellent
electron transporting characteristics, and thus may be used as
electron injecting materials or electron transporting materials
suitable for all-color fluorescent and phosphorescent devices, such
as red, green, blue, and white fluorescent and phosphorescent
devices. For example, the heterocyclic compounds may be efficiently
used as light-emitting materials of green, blue, and white
fluorescent devices. By using the heterocyclic compounds, organic
light-emitting devices having high efficiency, low driving voltage,
high brightness, and long lifespan may be prepared.
[0180] By way of summation and review, an anthracene derivative may
be used as a material for the organic emission layer. However,
organic light-emitting devices including such an organic emission
material may not have satisfactory life span, efficiency, and power
consumption characteristics.
[0181] The embodiments provide a heterocyclic compound having
improved electrical characteristics, charge transporting
capabilities, and light-emission capabilities.
[0182] While the present invention has been particularly shown and
described with reference to exemplary embodiments thereof, it will
be understood by those of ordinary skill in the art that various
changes in form and details may be made therein without departing
from the spirit and scope of the present invention as defined by
the following claims.
* * * * *